Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → Ethyl 3-[(4-bromo-3-methoxyphenyl)amino]-3-phenylacrylate

HRID 1879270Notes

Reaction equation

HRID 1879270 reaction equation
[CH3:1][NH:2][C:3]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[CH:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br:16][C:17]1[CH:23]=[CH:22]C(N)=[CH:19][C:18]=1[O:24][CH3:25].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>C(Cl)Cl>[Br:16][C:17]1[CH:23]=[CH:22][C:1]([NH:2][C:3]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:19][C:18]=1[O:24][CH3:25]

Participants

5

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 70182544-Bromo-3-methoxyanilineHCID 58005139Ethyl 3-(methylamino)-3-phenylacrylate

Product 1

HCID 58005168Ethyl 3-[(4-bromo-3-methoxyphenyl)amino]-3-phenylacrylateYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 112 and 4-bromo-3-methoxyaniline (1 eq.) in DCM (0.15 M) was added PPTS (1 eq.). The mixture was heated to reflux and stirred for one day. The mixture was cooled and the solids were removed by filtration and washed with dichloromethane. The filtrate was concentrated and purified by column chromatography (SiO2, PE:EtOAc with EtOAc from 1 to 15%) to give the title compound 113 (80%). 1H NMR (CDCl3) δ (ppm) 10.32 (br s, 1H), 7.32 (m, 5H), 7.20 (d, J 8.5, 1H), 6.19 (dd, J 8.5, 2.5, 1H), 6.11 (d, J 2.5, 1H), 5.03 (s, 1H), 4.21 (q, J 7.0, 2H), 3.50 (s, 3H), 1.32 (t, J 7.0, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureThe mixture was cooled
  4. customthe solids were removed by filtration
  5. washwashed with dichloromethane
  6. concentrationThe filtrate was concentrated
  7. custompurified by column chromatography (SiO2, PE:EtOAc with EtOAc from 1 to 15%)

Sources & evidence

ORD record
ord-ba52075cdee749418810762749488315
Source dataset
uspto-grants-2012_11
Patent number
US08314062B2

Reaction notes

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